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The Best Winter Getaways Near Chicago

By Laura Slowick | Nov 14, 2018

In the Chicago area, it isn’t uncommon to feel confined indoors during the long, chilly winters. While it’s more traditional to travel in summer, you may be surprised to discover that some of these getaways are actually more picturesque in winter. And if you’ve hired contractors to transform your home over the holidays, what better way to escape the noise than to get out of the house and find cheer and refreshment in nature’s abundant tranquility!


Family-Style Holiday Cabins in Wisconsin Dells

If your ideal Christmas involves cocooning yourself inside a rustic log cabin nestled in a pristine blanket of snow while sipping cocoa by the fire with family and friends, you can drive just over three hours to the Wisconsin Dells. Everyone knows Sand County as a popular summer resort scene, but in winter, the Dells transform into a quaint and charming scene worthy of a Thomas Kinkade painting. You can rent homes, cottages, condos, or cabins of all sizes. Did we mention that the Dells are also a famous destination for delicious dining? You can reserve your family-style holiday cabin getaway here.


Skiing and Snowboarding at Chestnut Mountain in Galena

While a mere change of scenery works wonders to beat the winter blues, some of us also seek more active ways to enjoy the holidays. Galena, IL’s Chestnut Mountain resort is under three hours away, and it’s got some of the best skiing and snowboarding slopes in the area. If you’re a professional, you’ll love the 3,500 feet of beautiful slopes, and if you’re an amateur, the variety of group, private, and semi-private lessons have got you covered. At the day’s end, you can soak in a jacuzzi or warm up in a sauna at the resort.


Relaxing at Grand Traverse Resort and Spa

Just under five hours away, the Grand Traverse Resort and Spa is a bit of a trek, but for a long weekend away, it’s worth it. Traverse City has a little bit of everything--it’s famous for its vineyards like Bower’s Harbor, its craft beer scene with destinations like Shorts Brew Pub, and its fine dining. On the resort itself, you can enjoy activities like winter golf, indoor water playgrounds and pools, spa treatments, shopping, ice skating, snowshoeing, and cross country skiing. Staying at the resort also gives you easy access to a local theater, sleigh rides, downhill skiing and tubing, snowmobile rentals, and more!

Romantic Getaway at the Inn at Bay Harbor

If you’re up for driving just North of Traverse City, you’ll find yourself at the stately Inn at Bay Harbor near Petoskey, MI. This stately inn overlooks Lake Michigan, whose shoreline is breathtakingly beautiful in winter. Take advantage of the full-service spa treatments or salon after exploring local boutique shopping. The Inn even offers a Romance Package, starting at just $190 a night, that’s perfect for anniversaries or just taking time to reconnect with your special someone away from the stresses of everyday life. 

Because Chicago is a destination city, it’s easy to habituate yourself to day trips within city limits. But part of what makes Chicago such a great place to live is that it’s centrally located near other destination cities and vacation resorts. So this winter, make the most of living in Chicago by exploring nearby gems that give you a change of scenery, a release for your cabin fever, and a chance to slow down and enjoy the season.

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